70107-41-4Relevant articles and documents
Convenient and easy access to 2-hydroxycyclopent-2-enones from acylcyanohydrins
Pantin, Mathilde,Bodinier, Florent,Saillour, Jordan,Youssouf, Yassine M.,Boeda, Fabien,Pearson-Long, Morwenna S.M.,Bertus, Philippe
, p. 4657 - 4662 (2019/07/16)
A convenient access to 2-hydroxycyclopentenones was designed from acylcyanohydrins, by using titanacyclopropane complexes as nucleophilic partners and an intramolecular aldol condensation in basic conditions. The development of a one-pot procedure allows a step- and atom-economic process, and the use of Grignard reagents other than ethylmagnesium bromide provided valuable 3,4-disubstituted 2-hydroxycyclopentenones. The utility of the hydroxy group was illustrated by further functionalization of the α-position using palladium-mediated cross-coupling reactions.
Titanium-mediated synthesis of 1,4-diketones from grignard reagents and acyl cyanohydrins
Setzer, Paul,Beauseigneur, Alice,Pearson-Long, Morwenna S. M.,Bertus, Philippe
supporting information; experimental part, p. 8691 - 8694 (2011/01/10)
Double duty: In the presence of titanium isopropoxide, Grignard reagents were found to react with acyl cyanohydrins to give substituted 5-hydroxy-1,4-diketones (see scheme). This new reaction involves a formal addition of a 1,2-dianion equivalent to both the ester and nitrile moieties.
Addition of Aldehydes to Activated Double Bonds, XXVIII. Preparations and Reactions of Alkoxy- and Acetoxy-2,5-diones
Stetter, Hermann,Mohrmann, Karl-Heinrich,Schlenker, Walter
, p. 581 - 596 (2007/10/02)
Thiazolium salt-catalyzed addition of aliphatic ether-aldehydes and pyrancarbaldehydes leads to corresponding 1-alkoxy-2,5-alkanediones 1-11 and pyranyl-1,4-alkanediones 28 - 47.In the same manner aldehydes react with 1-acetoxy-3-buten-2-one to give 1-acetoxy-2,5-alkanediones 12 - 19, which after saponification yield the 1-hydroxy-5-alkyl-2,5-pentanediones 20 - 27.